


Started With A Dare

by fidelissimi



Category: Supernatural
Genre: Bottom Dean, Bottom Dean Winchester/Top Sam Winchester, Butt Plugs, Come Eating, First Time, M/M, Rimming, Top Sam
Language: English
Status: Completed
Published: 2017-01-26
Updated: 2017-01-26
Packaged: 2018-09-20 00:42:51
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,729
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9467759
Author URL: https://archiveofourown.org/users/fidelissimi/pseuds/fidelissimi
Summary: Dean's first time bottoming. With a side of that special way the Winchesters say everything while saying nothing at all.





	

**Author's Note:**

> First published writing. Be gentle please. Kudos and comments are love.  
> Written for a prompt on Tumblr.

Sam slips the plug out of Dean that he’d dared him to wear for 24 hours, pulling gently on the flared end of the orange silicone until he can feel and hear the audible _pop_ as it’s freed from his brother’s body.

Dean’s eyes are screwed shut tight, breath quickened from the last 20 minutes he had to wear it and cock softening as the last dredges of a long-awaited and well earned orgasm roll through his body. Sam spent that time pushing and pulling on the base, twisting the plug while it rested inside of Dean, teasing at his prostate and seeing how many sounds he could pull from his brother’s lips. It was more than he even dared to think he could get, and his cock is about to break through his zipper because of those absolute sounds of sin.

Dean’s still white-knuckling the threadbare sheets under him, hips undulating against his will and the slightly stretched pucker of his hole clenching around air now that the plug is gone. He thought this dare would be torture of a different kind. The embarrassing and ‘unmanly’ kind, though usually he’s not one to kink shame. Dean just doesn’t bottom. Dean doesn’t even have sex with guys, but a dare is a dare and he couldn’t let Sammy win.

As his orgasm finally tapers off to nothing, he thinks to himself that he’s not actually sure who won this time. 

And Dean’s been able to keep his mouth shut about the massive amount of not-brotherly-feelings he’s had for Sam for as long as he can remember. He chalked it down to how close they grew up and how his brother is definitely not a bad looking dude (no matter how much he makes fun of him for his long hair and girly puppy dog eyes). That’s all it was, and he’s tried to make himself believe that. 

But this entire day, 24 entire fucking hours, has made it nearly impossible (because how goddamn sexually frustrated can you get from a tiny little silicone plug your brother dared you to wear?) and since Sam took every opportunity to jolt the car, hitting potholes and even driving through a parking lot with those awful speed bumps to deter kids from speeding and hitting pedestrians, Dean’s knows the answer to that question now ——— a LOT.

So it doesn’t help now that Sam, as he’d promised, helped Dean take the plug out, and he’s staring at his ass like he wants to eat him, licking his lips like he can already taste Dean there. And Dean’s completely taken aback when Sam pushes in with his shoulders, lowers his mouth to the empty space between Dean’s splayed thighs and presses a flat tongue over that winking hole. 

“The fuck are y— _oh_ _god_..” That’s as far as his protest goes. Sam’s lapping at him and sucking at the skin around his hole and Dean’s starting to chub up again already, this time maybe not so much against his will as it his just to his surprise. He doesn’t have to wonder long if this had been Sam’s plan all along, an ice-breaker on the notoriously deep pond of sorts, or if this is spur of the moment because in between the nips and bites to the tender skin of his ass cheeks Sam’s spilling out words like “ _waited so long to be right here”_  and “ _please Dean let me have this, let me inside, pleasepleaseplease.”_

Dean has never known how to tell his baby brother no — so he doesn’t.

In less time than it takes for him to nod and grunt his permission, Sam is stripping his shirt over his head and crawling up the bed, licking Dean’s release off his stomach and chest before lips press hard against his brother’s. He’s licking into Dean’s mouth, feeding the salty, musky and unique taste of Dean’s own come into his mouth and Dean’s sucking it off Sam’s ridiculously talented tongue like a life-giving serum. 

Sam throws up a thank you to whoever decided he was allowed to have arms long enough to reach off the side of the bed and snag a bottle of lube and a condom from his bag and stay lip locked with his brother the entire time. Fingers slicked, he sinks two directly into the soft, slightly loosened heat of him and Dean keens, releasing another sound he’ll deny for the rest of his fucking life. 

Sam’s thorough but quick in his prep, stretching his brother around three fingers, then four while he distracts him by sucking on the hinge of his jaw that he’s seen makes Dean lose his mind from when he brought back girls to their motel rooms as a teenager. 

Dean’s vision is blurred from the tears of absolute bliss building up in the corners of his eyes and he blinks them away long enough to find the condom Sam dropped by his head, tear into the wrapper with his teeth before grunting out, “Lose the fucking pants moron, c’mon Sammy.” He’s bossy even when he’s about to get fucked three ways from Sunday but Sam expects no less and obeys, pushing his jeans and boxer-briefs down long muscular legs and kicking them towards the other bed. Dean props up on an elbow, condom in hand when he finally gets an eye-full of what his brother is packing and he questions for a few seconds if Sam was thorough _enough_  working him open. 

Sam sees that flash of worry and pets over Dean’s thigh. “I’ll go slow. Be real careful, I swear.”

“I’m not a bitch, Sammy.” It’s the only way he knows to say _thank you._

He stretches the rubber over Sam’s massive erection and falls onto his back again, watching Sam dribble lube over his cock and smear it around, refusing to pay any attention to the warring emotions running through his mind telling him how _baddirtywrong_  this is, while feeling _perfectgoodright_ at the same time. Sam silences his thoughts with another kiss, softer this time, with only a little bite when he runs his teeth along Dean’s bottom lip. He lines up and pushes in slowly, just a couple inches at first, fully paying attention to the signals of _slow slow slow_  that Dean is emitting. And he does go slow, because it’s Dean’s first time bottoming, first time _ever_ with a guy as far as Sam’s aware, and he’s not going to hurt his brother. Never, never hurt Dean. Not like this. Not in any way.

Dean’s previously insistent erection flags partway, unaccustomed to this particular kind of pain, and a hand on Sam’s hip halts his forward progression and let’s Dean catch his breath. “Can’t believe girls actually let you fuck them with this monster. No wonder you never get laid.” 

Sam just grins. Then Dean’s pulling on that same hip to get Sam to keep going. It only takes a minute or two, and with an afterthought of getting his hand on his cock, tugging and twisting on the upstroke, he’s hard again and Sam is fully seated inside of him, still watching Dean’s face for the go ahead as his thighs rest gently against the skin of Dean’s ass.

Dean gives a nod, a silent “please” and Sam’s moving, urgency barely coloring his long, deep thrusts. His lungs burn, and his mind spins, but he keeps going, so glad Dean didn’t freak out. That yet again, even without a word, they were on the same page about something else, especially something like this.

They’re both so keyed up that neither of them will last long, and they both know it. More of that silently shared knowledge. Dean is so hot and tight around Sam that he feels like he’s trying to choke his life out through his dick. Sam’s big enough he barely has to work to brush over Dean’s prostate each time he pumps his hips forward and buries himself inside.

Dean can’t concentrate on anything besides how fucking _good_  this feels, how _right_ this is, and Sam picks up where Dean hand left his cock to cling to Sam like a life raft. Jerking his brother off in time with his own thrusts, Sam grits his teeth and throws his head back, feels the tingle and fire burst of need building at the base of his spine. Dean’s leaking all over his stomach and Sam can only barely breathe out, “I’m close, De,” still floating in the wonderful realization that Dean gave him this, this one thing he’ll never give to anyone else.

“Me too, Sammy. M-me too, _fuck_.” Sam adjusts a little on his knees, presses his free hand to the back of Dean’s thigh to open his hips up a little more and pistons in and out of his brother’s body, the smack of skin getting louder and louder, thrusting harder and harder until he comes, fills the condom with a grinding stutter of his hips and then looks down just in time to see Dean lose it too, all over his hand and up to his chest, ass clamping down around Sam’s hard length, squeezing rhythmically as his balls pull tight to his body. 

They’re still for what feels like years before Sam eases out carefully, strips the condom off, ties the end and tosses it towards the only trash can in the room. Dean’s sweating, panting, and completely ignoring the mess he’s just made all over himself, so Sam takes it upon himself to clean his big brother up with his tongue. Dean’s grins, his cock giving a valiant effort at interest but he ignores it, let’s Sam finish taking care of him before letting his overgrown little brother slide up beside him and wrap too long arms and legs around him, drawing up the sheet at the end of the bed and wrapping them both in it. 

Sam can feel Dean’s heart beating against his ear, _thrum thrum thrumming_ away, and he knows his own is synced perfectly with that rhythm. “So do you hate me? Think I’m some kinda freak?” Sam asks quietly, words barely whispered against the skin of his big brother’s chest.

Dean rolls his eyes and presses a kiss to Sam’s sweaty forehead. “Course not. And if you are, I guess I’m right there with ya.” Just like always.

**Author's Note:**

> Comments are love!


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